This relaxed two-week plan pairs Key West’s landmark sights, water views, and food with plenty of unhurried time. It keeps most outings within one area each day, uses step-free options where available, and flags places where you should confirm access before booking.
Budget
About $1,000–$1,800 per person for meals, listed admissions, and activities, excluding lodging, flights, and most local transport. Accessible vehicle hire, private transfers, and specialist excursions can increase the total substantially.
Best time to visit
November to April for milder, drier weather; book accessible accommodation and transport early. Summer is hotter and more humid, with greater storm and hurricane risk.
Old Town and the waterfront
Ease into Key West with compact Old Town sights and an accessible waterfront sunset.
Morning
Visit
Take in the harbour views and get oriented on the broad waterfront promenade. Surfaces and crowd levels vary, so allow extra time and ask staff about the easiest route.
FreeAfternoon
Explore the
It is about a 3-minute roll from . Call ahead to confirm the current step-free route and elevator access through the exhibits.
About About $20Evening
Watch sunset at
Return to the waterfront, about a 3-minute roll away. Arrive early for space and check the surface conditions before choosing a viewing spot.
Free
Truman Annex and Whitehead Street
See the presidential history and island’s most famous landmark in the quieter northern end of Old Town.
Morning
Tour the
Allow time for the guided visit and confirm accessible entry and tour arrangements before you go.
About About $25Afternoon
See the
It is about a 10-minute roll south along Whitehead Street. The queue can be long, and the area around the buoy may be uneven.
FreeEvening
Have dinner at
Roll about 5 minutes to this Bahama Village restaurant. Contact the restaurant in advance to confirm an accessible entrance, seating, and restroom details.
About $25–$45
Duval Street and Old Town
Keep the day central with an accessible museum visit and a relaxed dinner on Duval Street.
Morning
Explore the Ernest Hemingway Home and Museum
Ask the museum about its current accessible route and viewing options; the historic property has areas that may not be suitable for wheelchair access.
About About $19Afternoon
Visit the
It is about a 4-minute roll from the Hemingway home. The tower climb is stair-only, but ask staff about accessible exhibits and the grounds.
About About $17Evening
Dine at
Roll about 8 minutes through Old Town. Reserve ahead and verify the entrance, table layout, and restroom access.
About $30–$55
Fort Zachary Taylor and the southern shore
Spend a low-key day among the fort’s history and coastal scenery, with access details checked in advance.
Morning
Visit
Allow about 10 minutes by accessible taxi from central Old Town. Ask the park about accessible routes, beach equipment, and current path conditions.
About About $6 per vehicle, plus any applicable feesAfternoon
Relax at
Stay within the same park, a short roll from the fort area depending on your route. Sand can be difficult to navigate; check ahead about beach wheelchairs and mat access.
About Included with park admissionEvening
Have dinner at
Take an accessible taxi about 10 minutes back toward the harbour. Confirm step-free entry and accessible restroom arrangements when reserving.
About $40–$75
Bahama Village
Enjoy a neighbourhood-focused day with a local museum, nearby history, and a beloved casual meal.
Morning
Visit the
Take an accessible taxi about 8 minutes from central Old Town. Check the route and surface conditions before setting out.
FreeAfternoon
Explore the Key West Lighthouse area
Travel about 8 minutes by accessible taxi back toward Bahama Village. Confirm any museum access needs in advance; the lighthouse tower itself is stair-only.
About About $17Evening
Enjoy dinner at
It is about a 5-minute accessible taxi ride away. Call to check the entrance and restroom setup and to request suitable seating.
About $20–$40
Higgs Beach and White Street Pier
Pair a mellow coastal morning with a nearby garden and pier visit.
Morning
Spend time at
Take an accessible taxi about 8 minutes from central Old Town. Ask the city or beach staff about beach-wheelchair availability and the condition of accessible paths.
FreeAfternoon
Explore
Roll or travel about 5 minutes by accessible taxi from . The historic garden paths may be uneven, so check current access before visiting.
About DonationEvening
See the water from
It is about a 5-minute accessible taxi ride away. Check the pier’s current surface and access conditions, particularly after rough weather.
Free
Key West history and local flavours
Spend an easy day close to central Old Town, mixing island history with a taste of Cuban coffee and cooking.
Morning
Visit the
The museum is in the heart of Old Town. Contact the Custom House about elevator access and the step-free visitor route before your visit.
About About $18Afternoon
Stop for coffee at
Roll about 5 minutes toward the harbour. Check which location you are visiting and confirm its entrance and counter access.
About $5–$15Evening
Dine at
This restaurant is on Sunset Key; arrange the resort-operated boat transfer from the Key West waterfront and confirm accessible boarding and facilities before booking.
About $60–$120, plus any transfer charges
Stock Island
Venture a short distance east for harbour views, seafood, and a change of scene away from the busiest Old Town streets.
Morning
Explore
Take an accessible taxi about 15 minutes from central Key West. Confirm accessible routes across the marina and any venue-specific access before arrival.
FreeAfternoon
Have lunch at
It is about a 5-minute accessible taxi ride from the marina village. Call ahead about entrance access, seating, and restrooms.
About $20–$40Evening
See a show at
Return to central Key West by accessible taxi, about 15 minutes. Contact the box office when booking to reserve accessible seating and confirm entry details.
About $25–$70
Old Town gardens and architecture
Slow the pace with shady garden paths and a comfortable dinner in the historic centre.
Morning
Visit the
Take an accessible taxi about 8 minutes from central Old Town. Ask about firm, step-free paths, since garden surfaces can be uneven.
About DonationAfternoon
Tour the
Travel about 8 minutes by accessible taxi back to Old Town. The historic house may have limited access, so check the current accessible route and garden surfaces in advance.
About About $15Evening
Dinner at
Roll about 5 minutes through central Old Town. Reserve and confirm step-free entry and accessible restroom details.
About $35–$65
Marathon day trip
Take an accessible vehicle excursion to the Middle Keys for a major bridge view and a nature-focused stop.
Morning
Drive to the
Arrange a wheelchair-accessible vehicle for the roughly 1-hour drive from Key West. View the bridge from a safe, accessible pull-off; do not attempt to use the bridge walkway without checking current access and safety conditions.
About Transport variesAfternoon
Visit the Turtle Hospital
It is about a 10-minute drive from the bridge area. Book a tour and confirm wheelchair access, accessible parking, and restroom facilities directly with the hospital.
About About $30Evening
Return to Key West for dinner at
Allow about 1 hour by accessible vehicle back to Key West, then confirm entry and seating access with the restaurant before dinner.
About $40–$75
Old Town shopping and sweets
Keep the day flexible and central with a few classic island treats and time to browse.
Morning
Browse the
Take a gentle roll along the harbourfront and check the surface conditions as you go. Some sections can be busy or uneven.
FreeAfternoon
Try a slice at
Roll about 5 minutes from the seaport through Old Town. Confirm the entrance and seating arrangements at the shop.
About $5–$15Evening
Browse at sunset
It is about a 5-minute roll away. The square gets crowded near sunset, so arrive early and pick a spot with room to turn and maneuver.
Free
Accessible water outing
Make room for an on-the-water experience, choosing an operator only after confirming boarding and restroom arrangements.
Morning
Take an accessible harbour cruise
Depart from the . Operators and vessels vary, so book directly and confirm ramp or lift boarding, companion seating, and accessible toilets before paying.
About About $40–$80Afternoon
Have lunch at
It is a short roll from the seaport, about 3 minutes. Call ahead to confirm the entrance, table spacing, and accessible restroom.
About $25–$50Evening
Enjoy live music at
Take an accessible taxi about 8 minutes from the harbour. Ask about entrance access, crowd conditions, and suitable seating for the performance.
Free
Southern Old Town favourites
Revisit a favourite stretch of Old Town with a landmark, a quiet pause, and a relaxed meal.
Morning
Return to the
Go early to avoid the busiest queues. The spot is outdoors and free; check the pavement and curb cuts along your approach.
FreeAfternoon
Relax at the
Roll about 5 minutes from the buoy. Call ahead to confirm the current step-free entrance and route through the conservatory.
About About $18Evening
Dinner at
Travel about 8 minutes by accessible taxi toward the centre of Old Town. Reserve ahead and confirm accessible entry and restroom arrangements.
About $45–$80
A gentle final day in Old Town
Wrap up with easy waterfront time, a favourite bite, and one last Key West sunset.
Morning
Enjoy a relaxed breakfast at
Take an accessible taxi about 5 minutes within Old Town. Call ahead to confirm entrance and restroom access, and allow extra time for a leisurely meal.
About $20–$40Afternoon
Browse the
Travel about 8 minutes by accessible taxi or a longer roll depending on your starting point. The waterfront route is pleasant, but surfaces and crowds can vary.
FreeEvening
Close the trip at
Roll about 5 minutes from the seaport. Settle in before the sunset crowd arrives and enjoy the island’s familiar waterfront one last time.
Free
Good to know
Accessibility checks
Access can differ between entrances, rooms, vessels, and even day-to-day path conditions. Call each venue directly about step-free entry, door widths, accessible restrooms, seating, and any lift or ramp, rather than relying only on general listings.
Getting around
Key West is compact, but pavement, curb cuts, heat, and crowds can make rolling tiring. Arrange wheelchair-accessible taxis or a rental vehicle in advance; do not assume a standard taxi will have a lift.
Beach and boat access
Ask about beach wheelchairs and firm access mats before visiting the shore. For cruises and the Sunset Key restaurant transfer, confirm the vessel’s boarding method and onboard accessible facilities before booking.
Heat and pace
Plan outdoor stops early or near sunset, carry water, and leave room for rest breaks. The schedule is intentionally easy to swap around if the weather or energy levels call for a quieter day.
Costs
Prices are rough USD estimates per person and can change; restaurant totals vary with drinks and tip. Confirm current admission prices and reservations directly with each venue.